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The connection between Machiavelli’s career in the Florentine chancery (1498-1512) and his achieved political work is explicitly formulated in the dedication of The Prince. Many scholars have noticed that Machiavelli’s diplomatic letters and first writings anticipate the main themes characteristic of his political thought. However, the transition from experience to political « theory » is not so immediate. In his writing of political experience, Machiavelli resorts to the ritratto, which is composed of excerpts from the reality witnessed during his diplomatic missions. The ritratto is a critical questioning of political experience from the consideration of practical effects. Consequently, the experience on which the treaty of The Prince is based is not a copy of real-life facts, it is a sum of ritratti already shaped by the view of the political thinker, historian of the present. Thus, Machiavelli endeavours to rationalize political action through a never-ending conceptual undertaking based on particular events subjected to fortune.